Patents by Inventor Raymond Le Van Mao

Raymond Le Van Mao has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 11780797
    Abstract: This invention relates to a method for the conversion of lignocellulosic biomass into ethyl esters of carboxylic acids. Said method consists of treating the biomass material with an oxidizing agent that is incorporated in an solution comprising one or more acids, one or more alcohols and water, and subsequently performing a catalytic reaction at a higher temperature using the same acidic solution into which a larger volume of alcohol is added, in such a way that the catalytic conversion occurs in a medium with a much higher concentration of alcohol, i.e. with a much higher alcohol-to-water wt ratio. Such a method results in relatively high yields of ethyl esters, such as ethyl esters of formic, acetic, and levulinic acids, while producing a low yield of dialkyl ethers, which are unwanted by-products. The concentration of the oxidizing agent in the pre-treatment step is preferably higher than 6.0 wt %.
    Type: Grant
    Filed: February 1, 2022
    Date of Patent: October 10, 2023
    Assignee: 11127012 CANADA INC.
    Inventor: Raymond Le Van Mao
  • Publication number: 20220153680
    Abstract: This invention relates to a method for the conversion of lignocellulosic biomass into ethyl esters of carboxylic acids. Said method consists of treating the biomass material with an oxidizing agent that is incorporated in an solution comprising one or more acids, one or more alcohols and water, and subsequently performing a catalytic reaction at a higher temperature using the same acidic solution into which a larger volume of alcohol is added, in such a way that the catalytic conversion occurs in a medium with a much higher concentration of alcohol, i.e. with a much higher alcohol-to-water wt ratio. Such a method results in relatively high yields of ethyl esters, such as ethyl esters of formic, acetic, and levulinic acids, while producing a low yield of dialkyl ethers, which are unwanted by-products. The concentration of the oxidizing agent in the pre-treatment step is preferably higher than 6.0 wt %.
    Type: Application
    Filed: February 1, 2022
    Publication date: May 19, 2022
    Applicants: Les Exploitations J.Y.B. Papineau Inc., La Cooperative Forestiere Des Hautes Laurentides, Les Creations Madero Inc., 9078-0900 Quebec Inc.
    Inventor: Raymond Le Van Mao
  • Patent number: 11236038
    Abstract: This invention relates to a method for the conversion of lignocellulosic biomass into ethyl esters of carboxylic acids. Said method consists of treating the biomass material with an oxidizing agent that is incorporated in an solution comprising one or more acids, one or more alcohols and water, and subsequently performing a catalytic reaction at a higher temperature using the same acidic solution into which a larger volume of alcohol is added, in such a way that the catalytic conversion occurs in a medium with a much higher concentration of alcohol, i.e. with a much higher alcohol-to-water wt ratio. Such a method results in relatively high yields of ethyl esters, such as ethyl esters of formic, acetic, and levulinic acids, while producing a low yield of dialkyl ethers, which are unwanted by-products. The concentration of the oxidizing agent in the pre-treatment step is preferably higher than 6.0 wt %.
    Type: Grant
    Filed: March 22, 2017
    Date of Patent: February 1, 2022
    Assignees: La Cooperative Forestiere Des Hautes Laurentides, Les Exploitations JYB Papineau Inc., Les Creations Madero Inc., 9078-0990
    Inventor: Raymond Le Van Mao
  • Publication number: 20210078930
    Abstract: This invention relates to a method for the conversion of lignocellulosic biomass into ethyl esters of carboxylic acids. Said method consists of treating the biomass material with an oxidizing agent that is incorporated in an solution comprising one or more acids, one or more alcohols and water, and subsequently performing a catalytic reaction at a higher temperature using the same acidic solution into which a larger volume of alcohol is added, in such a way that the catalytic conversion occurs in a medium with a much higher concentration of alcohol, i.e. with a much higher alcohol-to-water wt ratio. Such a method results in relatively high yields of ethyl esters, such as ethyl esters of formic, acetic, and levulinic acids, while producing a low yield of dialkyl ethers, which are unwanted by-products. The concentration of the oxidizing agent in the pre-treatment step is preferably higher than 6.0 wt %.
    Type: Application
    Filed: March 22, 2017
    Publication date: March 18, 2021
    Inventor: Raymond Le Van Mao
  • Publication number: 20150045595
    Abstract: The invention provides a process for producing ethyl esters and hydrocarbons from lignocellulosic biomass materials. The process comprises two steps: the first step being an acid ethanolysis (solvolysis with ethanol) of the biomass in oxidizing medium; the second step being the catalytic conversion of the by-product diethyl ether and, optionally, light ethyl esters, into hydrocarbons over ZSM-5 zeolite catalyst. Cellulose, hemicellulose and part of the lignin are converted in the first step. The oxidizer used in this first conversion step is preferably and most preferably hydrogen peroxide activated by Fe (II) (Fenton-type reagent), and/or Ti (IV) ions. The final products may include ethyl levulinate (diesel-grade additive), light ethyl esters (ethyl formate and ethyl acetate), levulinic acid, succinic acid, methanol, gasoline-range hydrocarbons and C2-C4 hydrocarbons.
    Type: Application
    Filed: February 20, 2013
    Publication date: February 12, 2015
    Applicant: AC3B TECHNOLOGIES LTD.
    Inventor: Raymond Le Van Mao
  • Publication number: 20100285950
    Abstract: Co-catalysts comprising yttria-stabilized aluminum oxide having nickel oxide loaded thereon, their uses and methods of preparing are described. Also, hybrid catalysts comprising these co-catalysts along with main catalyst components, and their uses and methods of preparing are described. Monocomponent catalysts having nickel oxide loaded thereon, their uses and methods of preparing are also described.
    Type: Application
    Filed: June 17, 2008
    Publication date: November 11, 2010
    Inventor: Raymond Le Van Mao
  • Patent number: 7456128
    Abstract: Disclosed herein are cracking catalysts useful in the thermo-catalytic cracking (TCC)—formerly called selective deep catalytic cracking (SDCC)—of petroleum naphthas, gas oils and other heavy hydrocarbon distillates to selectively produce light olefins, said catalyst comprising mesoporous mixed oxides modified by the presence of inorganic compounds containing chemical elements selected from phosphorus, sulfur, chlorine and mixtures thereof, said catalyst being supported on yttria stabilized zirconium oxide and/or aluminum oxide. Preferably, the catalyst will have the the following formula: (a) MoO3 and/or WO3; (b) La2O3; (c) CeO2; (d) P, S or Cl; (e) ZrO2; (f) Y2O3. Also preferably, the catalyst will be combined with a material selected from an acidic crystalline (modified or not) zeolite, an acidic silica molecular sieve and an acidic alumina. Also disclosed are methods of making said cracking catalysts. The cracking catalysts can be used in both mono- and dual reactor configurations.
    Type: Grant
    Filed: April 29, 2005
    Date of Patent: November 25, 2008
    Assignee: Valorbec, S.E.C., Represented by The Gestion Valeo, S.E.C.
    Inventor: Raymond Le Van Mao
  • Publication number: 20080227628
    Abstract: Disclosed herein are mesoporous material derived from a parent zeolite. In an embodiment of the invention, the mesoporous material derived from a parent zeolite, has an internal volume greater than about 0.35 cc/g and a surface area greater than about 250 m2/g, the mesoporous material comprises micropores having a surface area and mesopores, wherein the surface area of the micropores in the mesoporous material is less than about 25% of that in the parent zeolite, wherein less than about 3% of the internal volume of the mesoporous material is provided by micropores and wherein the mesopores are essentially homogeneously distributed and form an essentially interconnected network. In another embodiment of the invention, the mesoporous material derived from an alumina-rich parent zeolite has an internal volume greater than about 0.
    Type: Application
    Filed: October 12, 2006
    Publication date: September 18, 2008
    Inventor: Raymond Le Van Mao
  • Patent number: 7135602
    Abstract: Provided herein is a method and apparatus for selective deep catalytic cracking of petroleum naphthas or other hydrocarbon feedstocks. The feed comprising the hydrocarbons to be cracked and steam, in well-defined proportions, is first sent into a precatalytic zone (Zone I) of a cracking reactor, preferably a tubular reactor. In a preferred embodiment, Zone I, contains beads of some catalytically mildly active porous material such as quartz or quartz doped with Cr—Al, is set at a temperature T1. The gas steam flows then through a catalyst bed, called Zone II, where the catalytic reaction takes place. Zone II is set at temperature T2 and contains a zeolite type catalyst, preferably ZSM5 zeolite or, most preferably, a hybrid zeolite catalyst.
    Type: Grant
    Filed: November 3, 2000
    Date of Patent: November 14, 2006
    Assignee: Valorbec Societe en Commandite
    Inventor: Raymond Le Van Mao
  • Patent number: 7098162
    Abstract: Provided herein are monocomponent and hybrid catalyst compositions for use in steam-cracking of hydrocarbon feeds to selectively produce light olefins. The catalyst compositions being characterized by a first catalytic component comprising oxides of aluminum, silicon, chromium, and optionally, oxides of monovalent alkaline metals, and further comprising a binder, preferably bentonite clay. Preferably, the catalyst compositions will comprise a catalytic component in accordance with the following formula: (a) SiO2·(b) A12O3·(c) Cr2O3(d) alk2O, with alk being a monovalent alkaline metal, preferably selected from sodium, potassium and lithium. The second catalytic component is selected from a crystalline zeolite or a silica molecular sieve. Also provided in the present invention are methods of making the catalyst compositions.
    Type: Grant
    Filed: July 27, 2001
    Date of Patent: August 29, 2006
    Assignee: Valorbec Societe en Commandite
    Inventor: Raymond Le Van Mao
  • Patent number: 7026263
    Abstract: Provided herein are hybrid catalysts that are used in the deep catalytic cracking of petroleum naphthas or other hydrocarbon feedstocks, for the selective production of light olefins, in particular ethylene and propylene and BTX aromatics. The hybrid catalysts of this invention contain a chemically treated microporous crystalline silicate such as the pentasil-type silicalite, a mesoporous silica-alumina or zirconium oxide co-catalyst, into which may be incorporated aluminum oxide, molybdenum oxide, lanthanum oxide, cerium oxide or a mixture of aluminum and molybdenum oxides, and an inorganic binder such as bentonite clay.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: April 11, 2006
    Assignee: Valorbec, Société en commandite
    Inventor: Raymond Le Van Mao
  • Publication number: 20040014593
    Abstract: Provided herein are hybrid catalysts that are used in the deep catalytic cracking of petroleum naphthas or other hydrocarbon feedstocks, for the selective production of light olefins, in particular ethylene and propylene and BTX aromatics. The hybrid catalysts of this invention contain a chemically treated microporous crystalline silicate such as the pentasil-type silicalite, a mesoporous silica-alumina or zirconium oxide co-catalyst, into which may be incorporated aluminum oxide, molybdenum oxide, lanthanum oxide, cerium oxide or a mixture of aluminum and molybdenum oxides, and an inorganic binder such as bentonite clay.
    Type: Application
    Filed: January 28, 2003
    Publication date: January 22, 2004
    Applicant: Concordia University
    Inventor: Raymond Le Van Mao
  • Publication number: 20030181323
    Abstract: Provided herein are monocomponent and hybrid catalyst compositions for use in steam-cracking of hydrocarbon feeds to selectively produce light olefins. The catalyst compositions being characterized by comprising oxides of aluminum, silicon, chromium, and optionally, oxides of monovalent alkaline metals, and further comprising a binder. Preferably, the catalyst compositions will comprise a catalytic component in accordance with the following formula: (a)SiO2.(b)Al2O3.(c)Cr2O3.(d)alk2 O, with alk being a monovalent alkaline metal. Most preferably, the oxides are present in the following proportions: (a)SiO2:50-95 wt %;(b)Al2O3:3-30 wt %;(c)Cr2O3:2-10 wt %;(d)alk2O:0-18 wt %. Most preferably, the alkaline metal will be selected from sodium, potassium and lithium. The binder will preferably be bentonite clay. In hybrid configuration, the first catalytic component is provided as described immediately above. The second catalytic component is selected from a crystalline zeolite or a silica molecular sieve.
    Type: Application
    Filed: May 7, 2003
    Publication date: September 25, 2003
    Inventor: Raymond Le Van Mao
  • Patent number: 6316379
    Abstract: Provided herein is are acidic Z5M-5 zeollte materials which are highly active and selective in the synthesis of methyl tert-butyl ether (MTBE) and similar ethers. The materials are obtained by the preparation method comprising the main steps of: i) impregnation of zeolites with fluorine species using ammonium fluoride as precursor, preferably with a F loading of ca.1.9×103 mol.g−1 of zeolite; and ii) stepwise activation in air at preferably 250° C. and then preferably at 300° C. to 500° C., preferably 450° C. The method is preferably applied to desilicated ZSM-5 zeolite and provides conversion rates to MTBE superior to those obtained with prior art commercial AMBERLYSF™ resin (gas phase reaction at 70-80° C.) is obtained. No by-products, commonly produced by prior art commercial organic resin catalyst, are detected in the product spectrum.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: November 13, 2001
    Assignee: Concordia University
    Inventor: Raymond Le Van Mao
  • Patent number: 6184167
    Abstract: Disclosed herein are thermally stable ZSM-5 zeolite materials. The novel materials having substantially uniform micropores narrower (about 0.49 nm) or wider (about 0.55 nm and above) than those of conventional ZSM-5 zeolite (0.52-0.54 nm). Also disclosed is a preparation method (desilication/reinsertion/stabilization or DRS) for converting conventional ZSM-5 zeolite materials to the thermally stable zeolite materials of the present invention. The method of the present invention comprises the steps of sequentially treating ZSM-5 zeolite with aqueous solutions of sodium carbonate and sodium hydroxide to obtain a desilication of the zeolite, reinserting some of the silicon species (mainly sodium orthosilicate and sodium pyrosilicate) which have been selectively removed from the zeolite framework during the desilication operation, and activating the resulting materials in air or in the presence of steam at high temperatures. The amount of the reinserted silicon species depends on the pore size wanted.
    Type: Grant
    Filed: February 10, 1999
    Date of Patent: February 6, 2001
    Assignee: Concordia University
    Inventors: Raymond Le Van Mao, David Ohayon
  • Patent number: 5780689
    Abstract: In accordance with the present invention, there is now provided a novel selective catalyst useful for the synthesis of methyl-tert-butyl ether (MTBE) or ethyl-tert-butyl ether (ETBE) prepared by reacting isobutene with methanol or ethanol, respectively. More specifically, the catalyst of the present invention comprises from about 0.5 to about 7% by weight of triflic acid (trifluoro-methanesulfonic acid, CF.sub.3 SO.sub.3 H, hereafter referred to as TFA) incorporated onto an acid form Y zeolite.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: July 14, 1998
    Assignee: Societe Quebecoise D'Initiatives Petrolieres
    Inventor: Raymond Le Van Mao
  • Patent number: 5135898
    Abstract: In accordance with the present invention, there is now provided a hybrid catalyst suitable for the aromatization of light paraffins and olefins, comprising a mixture of a pentasil type zeolite having the structure of ZSM-5 or ZSM-11, and a cocatalyst consisting of gallium oxide supported by an oxide selected from the group consisting of silica, alumina particles and chromium oxide particles.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: August 4, 1992
    Assignee: Societe Quebecoise D'Initiatives Petrolieres (Soquip)
    Inventors: Raymond Le Van Mao, Jianhua Yao
  • Patent number: 4975402
    Abstract: An aromatization catalyst is obtained by physical mixing of a pentasil type zeolite, for example H-ZSM-5 and a zinc oxide-alumina co-precipitate. The weight ratio of the zeolite to the co-precipitate ranges from 4.3 to 28.3. The Zn/Al atomic ratio in the co-precipitate may range from about 0.16 to 25.0. The composite catalyst yields greater amounts of aromatics, particularly BTX aromatics, when contacted with an olefinic and/or paraffinic feedstock than the respective zeolite alone.
    Type: Grant
    Filed: June 1, 1989
    Date of Patent: December 4, 1990
    Assignee: Concordia University
    Inventors: Raymond Le Van Mao, Louise Dufresne
  • Patent number: 4873392
    Abstract: There is provided a process for converting diluted ethanol to ethylene which comprises heating an ethanol-containing fermentation broth thereby to vaporize a mixture of ethanol and water and contacting said vaporized mixture with a ZSM-5 zeolite catalyst selected from the group consisting ofa ZSM-5 zeolite having a Si/Al atomic ratio of from 5 to 75 which has been treated with steam at a temperature ranging from 400.degree. to 800.degree. C. for a period of from 1 to 48 hours;a ZSM-5 zeolite having a Si/Al atomic ratio of from 5 to 50 and wherein La or Ce ions have been incorporated in a weight percentage of 0.1 to 1.0% by ion exchange or in a weight percentage ranging from 0.1 to 5% by impregnation, anda ZSM-5 zeolite having a Si/Al of from 5 to 50 and impregnated with a 0.5 to 7% wt % of triflic acid,and recovering the ethylene thus produced.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: October 10, 1989
    Assignee: Concordia University
    Inventor: Raymond Le Van Mao
  • Patent number: 4847223
    Abstract: There is provided a catalyst comprising from 0.5 to 7% by weight of trifluoromethanesulfonic acid incorporated onto an acid-form pentasil zeolite having a Si/Al atomic ratio ranging from 5 to 50 and a process for producing same. Also within the scope of the present invention is a process for the conversion of dilute aqueous ethanol to ethylene comprising: flowing said ethanol through a catalyst comprising from 0.5 to 7% by weight of trifluoromethanesulfonic acid incorporated onto an acid-form pentasil zeolite having a Si/Al atomic ratio range from 5 to 50 at a temperature ranging from 170.degree. to 225.degree. C. and recovering the desired product.
    Type: Grant
    Filed: April 8, 1988
    Date of Patent: July 11, 1989
    Assignee: Concordia University
    Inventors: Raymond Le Van Mao, Thanh M. Nguyen